WO2006030537A1 - Procédé servant à produire un produit durci de résine photosensible - Google Patents

Procédé servant à produire un produit durci de résine photosensible Download PDF

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Publication number
WO2006030537A1
WO2006030537A1 PCT/JP2004/014870 JP2004014870W WO2006030537A1 WO 2006030537 A1 WO2006030537 A1 WO 2006030537A1 JP 2004014870 W JP2004014870 W JP 2004014870W WO 2006030537 A1 WO2006030537 A1 WO 2006030537A1
Authority
WO
WIPO (PCT)
Prior art keywords
photosensitive resin
resin composition
group
photopolymerization initiator
cured
Prior art date
Application number
PCT/JP2004/014870
Other languages
English (en)
Japanese (ja)
Inventor
Yoko Tomita
Kei Tomeba
Hiroshi Yamada
Original Assignee
Asahi Kasei Chemicals Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Asahi Kasei Chemicals Corporation filed Critical Asahi Kasei Chemicals Corporation
Priority to US11/659,743 priority Critical patent/US20080063979A1/en
Priority to JP2006535017A priority patent/JP4627531B2/ja
Priority to EP04792167A priority patent/EP1801145B1/fr
Priority to DK04792167T priority patent/DK1801145T3/da
Priority to CN2004800439831A priority patent/CN101018819B/zh
Priority to DE602004017917T priority patent/DE602004017917D1/de
Publication of WO2006030537A1 publication Critical patent/WO2006030537A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41N—PRINTING PLATES OR FOILS; MATERIALS FOR SURFACES USED IN PRINTING MACHINES FOR PRINTING, INKING, DAMPING, OR THE LIKE; PREPARING SUCH SURFACES FOR USE AND CONSERVING THEM
    • B41N1/00—Printing plates or foils; Materials therefor
    • B41N1/12—Printing plates or foils; Materials therefor non-metallic other than stone, e.g. printing plates or foils comprising inorganic materials in an organic matrix
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/44—Polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/81—Unsaturated isocyanates or isothiocyanates
    • C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
    • C08G18/8116—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/12—Chemical modification
    • C08J7/16—Chemical modification with polymerisable compounds
    • C08J7/18—Chemical modification with polymerisable compounds using wave energy or particle radiation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C08L75/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/035—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyurethanes

Definitions

  • a method of coating the surface of the liquid photosensitive resin composition layer with a highly light-transmitting cover film, a method of photocuring in an inert gas atmosphere, a method of photocuring in the vacuum The liquid photosensitive resin composition layer has been cured by a method such as photocuring with a liquid. At that time, the liquid photosensitive resin composition is coated on a support to form a photosensitive resin composition layer, and then a cover film is coated on the surface, or the exposure atmosphere is inert such as vacuum or nitrogen.
  • a mechanism for forming a gas atmosphere or a water atmosphere is required, and an apparatus for photocuring the liquid photosensitive resin composition has a more complicated structure. Therefore, there has been a demand for a liquid photosensitive resin composition that can be cured in a thick film in the air.
  • Patent Document 7 a pattern is formed by exposing and developing after covering with a cover film, and on the formed pattern surface. It is generally known that the process of impregnating an organic carbonyl compound and irradiating light with a wavelength of 200 nm to 300 nm to reduce the tack of the surface of the cured product layer is performed separately. It is estimated that the method is applied.
  • the inventors of the present invention diligently studied and formed a radical polymerization type photosensitive resin composition layer containing a hydrogen abstraction type photopolymerization initiator and a decay type photopolymerization initiator on a sheet-like or cylindrical support. It was found that the photosensitive resin composition layer can be cured by forming and irradiating light in the atmosphere, and the present invention has been completed. That is, a combination of a hydrogen abstraction type photopolymerization initiator and a decay type photopolymerization initiator, or a photopolymerization start having a site functioning as a hydrogen abstraction type photopolymerization initiator and a site functioning as a decay type photopolymerization initiator in the molecule. By using an agent and a resin having a specific functional group, a surprising phenomenon has been found that a radical polymerization type liquid photosensitive resin composition layer can be photocured in a thick film state and in the air. It was.
  • An aromatic ketone is preferably used as the hydrogen abstraction type photopolymerization initiator (d).
  • this chemical reaction mechanism a chemical reaction mechanism has been proposed in which aromatic ketones are efficiently excited by photoexcitation into an excited triplet state, and this excited triplet state pulls out surrounding medium force hydrogen to generate radicals. The generated radicals are considered to be involved in the photocrosslinking reaction.
  • the hydrogen abstraction type photopolymerization initiator (d) may be any compound as long as it is capable of generating a radical by extracting the surrounding medium force hydrogen through the excited triplet state.
  • Thioxanthones refer to thixanthone and derivatives substituted with an alkyl group, a phenyl group, or a halogen group, and examples thereof include ethylthioxanthone, methylthioxanthone, and black-thick thixanthone.
  • Anthraquinones refer to anthraquinones and derivatives substituted with alkyl groups, phenyl groups, halogen groups, and the like.
  • the addition amount of the hydrogen abstraction type photopolymerization initiator is preferably 0.3 wt% or more and 10 wt% or less, more preferably 0.5 wt% or more and 5 wt% or less of the total amount of the photosensitive resin composition.
  • the decay-type photopolymerization initiator (e) refers to a compound that generates an active radical by a cleavage reaction occurring in the molecule after light absorption.
  • Specific examples include benzoin alkyl ethers, 2,2-dialkoxy 2-phenylacetophenones, acetophenones, acyloxymesters, azo compounds, organic compounds, and acylphosphine oxides. , Diketones and the like, and it is preferable to use at least one compound selected from these group forces.
  • the addition amount of the photopolymerization initiator (c) having a site functioning as a hydrogen abstraction type photopolymerization initiator and a site functioning as a decay type photopolymerization initiator in the same molecule is the total amount of the photosensitive resin composition. It is more preferably 0.5 wt% or more and 10 wt% or less, more preferably 0.5 wt% or more and 3 wt% or less. In this range, the mechanical properties of the cured product can be sufficiently secured even when the photosensitive resin composition is photocured in the air.
  • the resin (a) of the present invention comprises an aryl group, a linear or branched alkyl group substituted with at least one aryl group, another alkyl group, an alkoxy carbo group, a hydroxyl group in the molecule. Bonded to a carbon atom having at least one organic group selected from the group consisting of a formyl group, a carbonate bond or an ester bond, and the organic group or the bond being directly bonded It is preferable that the hydrogen atom ( ⁇ -position hydrogen) is 2% to 80% with respect to all hydrogen atoms in the molecule. The reason is not clear.
  • aryl groups include phenyl, tolyl, xylyl, biphenyl, naphthyl, anthryl, pyrenyl, and pentaryl groups.
  • the linear or branched alkyl group substituted with an aryl group is preferably, for example, a methyl styryl group or a styryl group.
  • the content of hydrogen at the ⁇ -position can be analyzed by nuclear magnetic resonance spectroscopy (NMR) focusing on hydrogen atoms.
  • NMR nuclear magnetic resonance spectroscopy
  • the compound having a plurality of groups is reacted with a binder having a plurality of functional groups capable of binding to the reactive group (for example, polyisocyanate in the case of a hydroxyl group-amino group) to adjust the molecular weight and to bind the terminal group.
  • the compound obtained by the reaction is reacted with a compound having a functional group and a polymerizable unsaturated group that reacts with the terminal binding group of this compound, and polymerized at the terminal.
  • Gender unsaturation A preferable method is a method of introducing a group.
  • the organic compound (b) of the present invention is a compound having an unsaturated bond involved in a radical polymerization reaction, and the number average molecular weight is considered in consideration of ease of dilution with the resin (a). Is preferably 100 or more and 1000 or less.
  • organic compounds include olefins such as ethylene, propylene, styrene, and dibenzene, acetylenes, (meth) acrylic acid and derivatives thereof, haloolefins, and unsaturated-tolyls such as acrylonitrile, (meth) acrylamide.
  • a polymerization inhibitor an ultraviolet absorber, a dye, a pigment, a lubricant, a surfactant, a plasticizer, a fragrance, and the like can be added to the photosensitive resin composition of the present invention according to the use and purpose. .
  • a cushion layer having an elastomer strength can be formed below the photosensitive resin cured product layer. Since the photosensitive resin cured product layer formed in the present invention has a thickness of 50 m-5 Omm, other lower layers may be made of materials having different compositions.
  • the tack layer is preferably an elastomer having a Shore A hardness of 10 to 70 degrees or an ASKER-C hardness of 20 to 85 degrees as measured with an ASKER-C hardness tester. When the Shore A hardness is 10 degrees or more, or the ASKER-C hardness is 20 degrees or more, the print quality can be ensured because it deforms appropriately.
  • the photocurable elastomer a mixture of the thermoplastic elastomer with a photopolymerizable monomer, a plasticizer, a photopolymerization initiator and the like, a liquid resin with a photopolymerizable monomer, a photopolymerization initiator, and the like.
  • the thermoplastic elastomer a plasticizer, a photopolymerization initiator and the like, a liquid resin with a photopolymerizable monomer, a photopolymerization initiator, and the like.
  • a liquid resin with a photopolymerizable monomer a photopolymerization initiator, and the like.
  • examples thereof include a mixed liquid photosensitive resin composition.
  • a modified layer on the surface of the photosensitive resin cured product layer of the present invention, it is possible to reduce tack on the surface of the printing substrate and improve ink wettability.
  • the modified layer include a film treated with a compound that reacts with a surface hydroxyl group such as a silane coupling agent or a titanium coupling agent, or a polymer film containing porous inorganic particles. Can do.
  • the compound constituting the silane coupling agent of the present invention contains, as a reactive functional group in the molecule, an alitaroyl group, a methacryloyl group, an active hydrogen-containing amino group, an epoxy group, a vinyl group, a perfluoroalkyl group, and a mercapto group.
  • a reactive functional group in the molecule an alitaroyl group, a methacryloyl group, an active hydrogen-containing amino group, an epoxy group, a vinyl group, a perfluoroalkyl group, and a mercapto group.
  • titanium coupling agents include isopropyl triisostearoyl titanate, isopropyl tris (dioctyl pyrophosphate) titanate, isopropyl tri (N-aminoethylaminoamino) titanate, tetraoctyl bis (ditriol).
  • a method of irradiating light in the vacuum ultraviolet region with a wavelength force of S 200 or less such as a xenon excimer lamp, or a method of exposing to a high energy atmosphere such as plasma, etc.
  • a hydroxyl group can be generated on the surface of the printing substrate, and the force coupling agent can be fixed at high density.
  • dyes examples include poly (substituted) phthalocyanine compounds and metal-containing phthalocyanines.
  • pigments include carbon black, graphite, copper chromite, chromium oxide, cobalt chrome aluminate, dark inorganic pigments such as copper oxide and iron oxide, and metal powders such as iron, aluminum, copper, and zinc. Examples include metals doped with Si, Mg, P, Co, Ni, Y, etc. These dyes and pigments may be used alone, in combination, or in any form such as a multilayer structure. However, in the case of a system that uses light to cure the photosensitive resin composition, the amount of the organic Z inorganic compound that absorbs a large amount of light at the wavelength of the light used for curing is within a range that does not affect photocurability.
  • the addition ratio with respect to the total amount of the photosensitive resin composition is preferably 0.01 wt% or more and 5 wt% or less, more preferably 0.01 wt% or more and 2 wt% or less.
  • Laser engraving is performed in an oxygen-containing gas, generally in the presence of air or in an air stream, but can also be performed in a carbon dioxide gas or a nitrogen gas.
  • Relief printing plate obtained by engraving, powdery or liquid substance slightly generated on the surface is washed with an appropriate method such as water containing solvent or surfactant, water-based cleaning agent by high pressure spray etc. It may be removed by using a method of irradiating with high pressure steam or a method of irradiating with high pressure steam.
  • the viscosity of the photosensitive resin composition was measured at 20 ° C. using a B-type viscometer (trademark, B8H type; manufactured by Tokyo Keiki Co., Ltd., Japan).
  • the number average molecular weights of rosin (a) and organic compound (b) were determined by conversion to polystyrene having a known molecular weight using gel permeation chromatography (GPC method).
  • GPC method gel permeation chromatography
  • HLC-8020 high-speed GPC device
  • TSKgel GMHXL polystyrene packed column
  • THF tetrahydrofuran
  • an ultraviolet absorption detector was used for rosin (a), and 254 nm light was used as monitor light.
  • the organosilicon compound (c) was detected using a parallax refractometer. Examples or ratios of the present invention
  • the resin (a) and organosilicon compound (c) used in the comparative examples had a polydispersity (MwZMn) determined using the GPC method greater than 1.1, so the number average molecular weight determined using the GPC method Mn was adopted. Since the organic compound (O) had a polydispersity (MwZMn) determined using the GPC method of less than 1.1, the molecular structural force and molecular weight identified using the NMR method were increased.
  • the obtained photosensitive resin composition was formed into a sheet having a thickness of 2.8 mm on a PET film, and exposed in the atmosphere using a trade mark ALF type 200UP post-exposure machine manufactured by Asahi Kasei Corporation.
  • a sheet-like photosensitive cured product was produced.
  • the light used for the exposure was ultraviolet fluorescent lamp (chemical lamp, center wavelength: 370 nm) 4000 mjZcm 2 and germicidal lamp (germisidal lamp, center wavelength: 253 nm) 12000 mjZcm 2 .

Abstract

L'invention concerne un procédé servant à produire un produit durci d'une résine photosensible, comprenant les étapes consistant à former une couche de composition de résine photosensible ayant une épaisseur qui n'est pas inférieure à 50 µm et qui n'est pas supérieure à 50 mm en utilisant une composition de résine photosensible contenant un initiateur de photopolymérisation de type à élimination d'hydrogène (d) et un initiateur de photopolymérisation de type à désintégration (e) ou un initiateur de photopolymérisation (c) ayant dans la même molécule un site qui sert d'initiateur de photopolymérisation de type à élimination d'hydrogène et un site qui sert d'initiateur de photopolymérisation de type à désintégration, et à irradier la couche de composition de résine photosensible avec de la lumière dans de l'air pour durcir la couche de composition de résine photosensible.
PCT/JP2004/014870 2004-09-13 2004-10-07 Procédé servant à produire un produit durci de résine photosensible WO2006030537A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US11/659,743 US20080063979A1 (en) 2004-09-13 2004-10-07 Process For Producing Cured Product Of Photosensitive Resin
JP2006535017A JP4627531B2 (ja) 2004-09-13 2004-10-07 感光性樹脂硬化物の製造方法
EP04792167A EP1801145B1 (fr) 2004-09-13 2004-10-07 Procede servant a produire un produit durci de resine photosensible
DK04792167T DK1801145T3 (da) 2004-09-13 2004-10-07 Fremgangsmåde til fremstilling af et hærdet produkt af lysfölsomt resin
CN2004800439831A CN101018819B (zh) 2004-09-13 2004-10-07 制备光敏树脂的固化产物的方法
DE602004017917T DE602004017917D1 (de) 2004-09-13 2004-10-07 Verfahren zur herstellung eines gehärteten produkts aus lichtempfindlichem harz

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2004265446 2004-09-13
JP2004-265446 2004-09-13

Publications (1)

Publication Number Publication Date
WO2006030537A1 true WO2006030537A1 (fr) 2006-03-23

Family

ID=36059804

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2004/014870 WO2006030537A1 (fr) 2004-09-13 2004-10-07 Procédé servant à produire un produit durci de résine photosensible

Country Status (9)

Country Link
US (1) US20080063979A1 (fr)
EP (1) EP1801145B1 (fr)
JP (1) JP4627531B2 (fr)
CN (1) CN101018819B (fr)
AT (1) ATE414732T1 (fr)
DE (1) DE602004017917D1 (fr)
DK (1) DK1801145T3 (fr)
ES (1) ES2314459T3 (fr)
WO (1) WO2006030537A1 (fr)

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US8268533B2 (en) * 2006-12-20 2012-09-18 Agfa Graphics Nv Flexographic printing forme precursor for laser engraving
WO2013015354A1 (fr) * 2011-07-28 2013-01-31 富士フイルム株式会社 Composition de résine pour une gravure au laser, précurseur de plaque d'impression en relief pour une gravure au laser, procédé de fabrication d'un précurseur de plaque d'impression en relief pour une gravure au laser, procédé de fabrication d'une plaque d'impression en relief et plaque d'impression en relief
CN108329645A (zh) * 2018-02-01 2018-07-27 上海交通大学 一种紫外光诱导梯度结构的杂化材料、制备方法及其在响应性形状转变方面的应用
JP2019518631A (ja) * 2016-05-24 2019-07-04 フォルクスヴァーゲン アクチエンゲゼルシャフトＶｏｌｋｓｗａｇｅｎ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ 注型材料、注型材料の製造方法、電子部品および自動車
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US20080053326A1 (en) * 2006-08-29 2008-03-06 Anderson Vreeland Inkjet composite stereographic printing plate and method for producing such printing plate
EP2095969B1 (fr) * 2006-12-18 2015-04-29 Toyobo Co., Ltd. Plaque originale d'impression gravable au laser
WO2008078699A1 (fr) 2006-12-26 2008-07-03 Asahi Kasei E-Materials Corporation Composition de résine pour une plaque d'impression
US8236479B2 (en) * 2008-01-23 2012-08-07 E I Du Pont De Nemours And Company Method for printing a pattern on a substrate
JP5241252B2 (ja) * 2008-01-29 2013-07-17 富士フイルム株式会社 レーザー彫刻用樹脂組成物、レーザー彫刻用レリーフ印刷版原版、レリーフ印刷版及びレリーフ印刷版の製造方法
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ATE414732T1 (de) 2008-12-15
CN101018819B (zh) 2011-12-07
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